Oh The Places You'll Go
by sunshine102897
Summary: When he went to sleep, he was resting comfortably in his Baby. Waking up is a whole other story as he finds himself trapped...in an airplane? Sam is gone. His own hair is too long. And he didn't remember his last name ever being Wesson. Set Season 5/ Season 1 AU


**_A/N: Set in Season 5...though the time frame is mostly 2005. You shall soon understand._**

 ** _Disclaimer: These lovely boys are unfortunately not mine. Sad face._**

 ** _Ding ding_** **. Passengers are advised to remain seated as we are experiencing slight turbulence as we pass over the mountains. If you have any questions or concerns, press the help button located directly under your seat. Thank you.**

Dean woke with a start at the strange automated voice overhead. He cracked his eyes open then brought his hands up to wipe away the blurriness. A yawn broke through, stretching his mouth wide as what resembled a growl escaped. Finally able to see clearly enough through his long, dark eyelashes he realized very quickly that he was not where he had been when he went to sleep. Meaning that the headrest behind him certainly wasn't black leather and that fruity scent most definitely was not whiskey and gunpowder. _...the hell?_ Senses on high alert, he propped himself up in the seat, which appeared to be some kind of white pleather, and took a good look around. _Definitely not the Impala. Where is Sam?_

 _Okay, first thing on today's to-do list, figure out how in the hell I got here._ To him it looked like some kind of plush seating hallway, with... _Is that a flight attendant?_ The perky brunette with a form fitting navy dress slightly turned, her equally perky face lighting up more as she caught his gaze.

"Can I help you with anything, sir? More wine, or maybe a pillow to make you more comfortable?" she beamed.

"Uh. Um. N-no thanks." _Way to go Dean. Stammering like an idiot._ As she turned to make her way back up the aisle he caught a fleeting glance at the label on her collar, which read in a fancy, red scroll, **American Airlines: First Class.** _No no no no no. This has gotta be some kinda nightmare induced by...uh...that airport we passed by on the way to Greenville. That's gotta be it._ Glancing around some more, he swallowed heavily. _Sure as hell feels real though._ Looking out the minuscule window and seeing nothing but clouds brushing past, he though he might have accidentally booked a return trip to Hell.

Dean was wedged between two women. To his right was what looked like a well-manicured soccer mom. She was full figured with a harsh black ponytail and even more severe gray eyes behind steel framed glasses. He would hazard a guess at early forties, unmarried, with no kids. Soccer mom yet not. She seemed more the type to carry around one of those yappy little rat dogs. Door number two, to his left, was a chick considerably more easy on the eyes. Long, low lighted blond hair cascaded off the shoulders of an unfairly modest blouse, though her skirt on the other hand didn't leave much to the imagination. She was thin, and if he had one word for her, he would say model-esque. _I don't even think that's a word. Oh well._ The model thing unfortunately came with a face caked with make-up.

It's not often the great Dean Winchester isn't familiar with his surroundings, but when it does happen, there seems to be a pattern.

Knocked out by bad thing. Said bad thing drags unconscious Dean away. Dean wakes up somewhere dark, dank, and mildly scary. Dean finds a way out, ensures his geeky little brother did not also fall into bad things hands. Kick ass, kill bad thing, grab little brother, then drive off into the sunset. (Okay, maybe that doesn't happen all the time, but close enough.) But all in all, it doesn't phase him.

This, on the other hand, was kinda scaring him. Sure, he doesn't exactly mind waking up not dying or in a situation with all signs pointing to imminent death, but he tends to feel more comfortable with what he knows best. In that case, having neon signs pointing to imminent death upon immediately prying open his eyelids. Waking up in a cushy seat next to a hot girl can only mean one thing: danger is lurking in the distance, laying in wait to come up and bite you in the ass when you think everything is all fine and dandy. Dean Winchester knows better. _Yeah, because you are Mr. Confidence._ If you are going to just wait around for everything to go to Hell in a handbasket, you might as well have a cushioned seat and headrest. _Better than being puppy chow your last seconds on Earth, that's for sure._

Twenty minutes later, he decided that Hellhounds were a better way to go. A thousand times better than this dragged out agony in which every shake and shift of the plane made him want to just grab the nearest patron's cocktail fork and end it all. _Okay Dean. Don't panic. You are only up in a flying metal death box sitting next to two chicks you don't recognize and are wearing a frigging monkey suit. An itchy monkey suit no less. Oh yeah, and the last time you were awake you were sitting being the dash of your car. No reason to panic. None. At. All._

He attached himself the arm rests, and took a deep breath. A deep, deep breath. One that was supposed to calm him the hell down but his luck had run out. _You fight monsters and ghosts and demons. You have been to Hell. Get a damn grip._

He cleared his throat, alerting the attention of the blond, who had previously been looking down at her magazine.

"Excuse me, miss. Um, I must have had a little too much to drink. Where is this plane headed, because I really hope its home."

A small smile quickly grew into a blinding grin on the hot chick's face.

"Ha-ha. Very funny, Dean. Now I know you didn't wanna do this shoot with Luke, but come on, the front cover of Status Magazine? I know you're excited," she hummed, reaching over and giving a cheek peck.

 _Oh crap. Double crap. I'm supposed to know who she is. Jesus. Front cover of what, now?_

"Uh. Yeah. Totally just screwing around. Humor me...sweetheart." _Okay. Play it safe until you figure out her name. We land, I am high tailing it outta here with the nearest car I can find._

Blond chick seemed to ignore Dean's desperation as she turned her gaze to the high class soccer mom on the right. "Hey, Dana? Can you review our schedule for tomorrow? I'm just wondering if Dean and I could squeeze in a little...down time." A mischievous little grin curled the girl's lips as her hand very slyly worked its way around his neck. _Okay. I certainly don't mind this._

Soccer mom pulled from her well-pressed navy jacket pocket what looked like a phone. That was outdated about five years. _Wishful thinking. Maybe she likes old school._

"Uh, let's see," she droned, scrolling down the illuminated screen with a silver stylus. "At 8 he has an interview with Glacier Magazine in Pasadena. 10:30 there's a signing at the Revel Theatre in L.A. Then at 2 we have to be in Huntington Beach for make up and wardrobe for the shoot. 6:30 we have reservations for La Restaurante in Oceanside, but we have to make it back to L.A by 9 for the next signing. Looks like your 'down time' might have to be scheduled for another day, Collette," she finished. He wouldn't be surprised if she just cut to the chase and turned up her nose. _Jesus, what the hell is all of this? A freaking schedule? A shoot?_ A sudden, very horrifying thought paraded into his mind. _Oh, God. I think I'm supposed to be a model. And there, my friends, is the resounding echo of the other shoe dropping._

The rest of the plane ride went about how you would expect it. A lot of deep breaths. An entire Metallica album hummed. And a complete internal freak out.

Dean was three seconds from getting on his knees and kissing the ground when they were allowed off the plane, but the blond chick-sorry, _Collette-_ refused to let go of his arm. Sure, he didn't mind it at first, but good God, woman. You would think she was permanently attached. Dean didn't do clingy. Like, _at all._ The last one who did that was that waitress in Des Moines who he swore he was gonna cut loose before they even got to his motel room. She clung to his arm like one of those creepy little suckerfish.

They just got out of that weird tunnel thing that connected the plane and the airport when a herd of Buffalo came stampeding toward them. A herd of Buffalo with about a thousand flashing lights going off.

"Mr. Wesson, Mr. Wesson!"

"Dean, over here!"

"What is it like being the most sought after model in the U.S?"

"Mr. Wesson, can you address the engagement rumors!?"

 _Yep. Definitely in Hell. My name isn't even Winchester._

He kept his head down and kept walking straight ahead, hoping beyond hope that he would wake up some time because he couldn't take being a circus clown anymore. _I said it once. I will say it again. I need to get the hell outta here and back to reality._

"Honey, where are you going? We need to answer these nice people's questions!" Collette pouted with a full on, puckered bottom lip. _Attention whore._

"I'm really, really tired, Collee-Collette. I just wanna get out of here," he growled, dragging his fingers up to rub across his forehead and pushing full speed ahead.

Of all the messed up, crazy situations he had landed himself in, this had to be the absolute worst. Not only was he being paraded around like some pampered pooch at the National Dog Show, he was forced into wearing starched, too tight slacks and a button down that was making his skin want to crawl out of it. Sam was no where in sight. He was going to be chauffeured in some ritzy, piece of crap car. All in all, he was miserable. Model dude wasn't even allowed a freaking phone call, because "Honey, Dana takes all your phone calls." Celebrity model, you say? More like Death Row inmate. _Yep. That would definitely be better._

After being followed by the annoying entourage of flash happy paparazzi, Dean was stuffed inside of a car that should've been bigger on the inside. Like, way, way bigger, so Clingy Collette wouldn't have to sit on his freaking lap.

"Oh, sweetheart," she purred, stroking his hair that was alarmingly long, "You look tired, baby. You want me to call room service when we get to the hotel, order some champagne? Send up a masseuse?"

It literally took all of his remaining effort not to roll his eyes. "Champagne? That bubbly, gay drink? No way, _sweetheart_. The only thing I will be drinking tonight is whiskey. And the only thing that will be touching my back is my bed, when I get into it," he finished resolutely.

"Dean! Since when do you drink whiskey? You are not allowed anything more alcoholic than champagne before photo shoots, you know that!" she shrieked full blast into his ear. _When she was sitting all quiet and oblivious of my panic attack, I liked her so much better._

"What has gotten into you, Dean?" Dana piped up, after having been encapsulated by her phone for the past 20 straight minutes. "First it looked like you were having a panic attack on the plane, sweating like a pig. Then ignoring the paparazzi? You always eat up the attention!" Her eyes suddenly widened. "Are you on drugs?" _For the love of-_

"Oh, God! You are!" Collette shrieked, yet again, her entire plastic surgery ridden face going almost comically pale before he even got a word in for defense. Not that he could give much. For all he knew the yuppy model dude that he was thrown in could be into the hard stuff. _Worth a try._

"No, I'm-"

"Ever since the plane you haven't been yourself. Baby, I know you've been under a lot of stress with dealing with your brother and all-" In a split second, Dean grasped onto Collette's arms tightly, pinning her against the car door as a sudden spike of fear ran through him like lightning. _What the hell kind of brother am I? He could be in this world too! I should've asked sooner, or, or done something!_ He was planning on calling Sam as soon as they got to wherever they were going, assuming he could get Dean out of whatever he had stepped in, but it looked like Sam might have stepped in it too.

"Ow! Baby, you're hurting me!"

"What's wrong with my brother? Where is he?" Collette turned frightened eyes over to Dana, who was looking a bit uncomfortable herself. He followed her gaze and set his eyes coldly onto Dana.

"Where. Is. My. Brother."

"Dean, he's in the same place he's been the past year and a half. The Colorado State Psychiatric Hospital. You must be on something pretty heavy to not remember that," Dana spat. Dean, however, didn't hear any bit of the last part, as his stomach took a nose dive. _Sammy? Why? Why would Sammy be there?_ He didn't want to ask, but he had to know. He cleared his throat, trying to find his voice again as he gradually released his grasp from Collette and sunk back into the seat.

"Why is Sammy there?" he whispered, barely audible over the drone of the car's engine. Dana raised a perfectly penciled eyebrow at Dean's labeling of his brother as 'Sammy.'

"Dean, he was placed there after he tried to kill himself almost two years ago."

 **I don't know what this sounds like, but I do know where it's going.**


End file.
